1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose

Base Information

• Chemical Name: 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose
• CAS No.: 149656-26-8
• Molecular Formula: C₂₉H₃₄O₄SeSi
• Molecular Weight: 553.632

Synonyms:1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose

Chemical Property of 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose

There total 7 articles about 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-ol + acetic anhydride (108-24-7) → 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose (149656-26-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jo00040a031

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose (149656-26-8)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide

3: diisobutylaluminum hydride / toluene / -78 °C

4: pyridine, 4-(dimethylamino)pyridine / 0 °C

With pyridine; 1H-imidazole; dmap; diisobutylaluminium hydride; In N,N-dimethyl-formamide; toluene;

DOI:10.1080/07328319808004670

Reference yield:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → 1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-(phenylselenenyl)-D-erythro-pentafuranose (149656-26-8)

Guidance literature:

Multi-step reaction with 3 steps

2: diisobutylaluminum hydride / toluene / -78 °C

3: pyridine, 4-(dimethylamino)pyridine / 0 °C

With pyridine; dmap; diisobutylaluminium hydride; In toluene;

DOI:10.1080/07328319808004670

upstream raw materials:

acetic anhydride

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-D-erythro-pentonic acid γ-lactone

Downstream raw materials:

N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-3-deoxy-2-Se-phenyl-2-seleno-β-D-erythro-pentofuranosyl>cytosine

3'-Deoxythymidine

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pentofuranosyl>thymine

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>thymine

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